The areas they are proposing are exactly within my desired neighbourhoods.

Your question about whether you should fix-up to sell, or sell as-is, isn't quite a cut-and-dry question as you're desired timeline to sell and your available cash come into play.  

Do to her age and desiring to be hands off, she has kept the same family in the property for nearly a decade at 1/4th the market rate.

All were surprised there's a desire to create a HOA.  

I am looking into doing business in Chicago because my father has a contracting business up there and would like to help him expand it and ultimately grow this empire that everyone here i'm sure desires.

Let me add that he is a fanatic about maintenance, etc, and his units are very desirable.

and start with making sure the lender can meet those needs or at least verify if they'll consider your desires as important. 

You have to register with code enforcement, include an addendum in your lease that has something to do with criminal activity on your property (I didn't read it and didn't make my tenant sign it), and sign a clause stating you will allow code enforcement, or as I like to call them government agents, come onto the property to look for code violations AND inspect the inside of the house if they desire.

Only a few blocks can make a huge difference in price and rent desirability. 

I know how to market very well and believe with some creativity I can make this place a desired place.